Abstract
The recognition ability of pyridinyl hydrazone derivatives of cone- and 1,3-alternate tetrathiacalix[4]arenes towards transition and alkali metals has been investigated by picrate extraction method. The stoichiometry of complexes and the extraction constants have been determined. It has been found that hydrazones do not extract alkali metal ions but show an excellent affinity towards transition and heavy metal cations. The removal of tert-butyl groups from calix[4]arene platform in the case of cone and 1,3-alternate isomers leads to an increase of d-ion extraction selectivity or efficiency.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Mahmoud, M.E., Osman, M.M., Hafez, O.F., Elmelegy, E.: Removal and preconcentration of lead (II), copper (II), chromium (III) and iron (III) from wastewaters by surface developed alumina adsorbents with immobilized 1-nitroso-2-naphthol. J. Hazard. Mater. 173, 349–357 (2010)
Quintelas, C., Rocha, Z., Silva, B., Fonseca, B., Figueiredo, H., Tavares, T.: Removal of Cd(II), Cr(VI), Fe(III) and Ni(II) from aqueous solutions by an E. coli biofilm supported on kaolin. Chem. Eng. J. 149, 319–324 (2009)
Knothe, G.: Some aspects of biodiesel oxidative stability. Fuel Proces. Technol. 88, 669–677 (2007)
Aydin, F.A., Soylak, M.: Separation, preconcentration and inductively coupled plasma-mass spectrometric (ICP-MS) determination of thorium(IV), titanium(IV), iron(III), lead(II) and chromium(III) on 2-nitroso-1-naphthol impregnated MCI GEL CHP20P resin. J. Hazard. Mater. 173, 669–674 (2010)
Vergel, C., Mendiguchía, C., García-Vargas, M., Moreno, C.: Quantification of free and bound fractions of nickel in naturalwaters by solvent extraction with 1, 2-cyclohexanedione bis-benzoyl-hydrazone. Solvent Extr. Ion Exch. 28, 625–635 (2010)
Schrader, T., Hamilton, A.D. (eds.): Functional synthetic receptors. Wiley-VCH, Weinheim (2005)
Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J. (eds.): Calixarenes 2001. Kluwer Academic Publishers, Dordrecht (2001)
Vicens, J., Harrowfield, J. (eds.): Calixarenes in the nanoworld. Springer, The Netherlands (2007)
Gutsche, C.D.: Calixarenes: An introduction, 2nd edn. The Royal Society of Chemistry, Cambridge (2008)
Podyachev, S.N., Syakaev, V.V., Sudakova, S.N., Shagidullin, R.R., Osyanina, D.V., Avvakumova, L.V., Buzykin, B.I., Latypov, Sh.K., Habicher, V.D., Konovalov, A.I.: Synthesis of new calix[4]arenes functionalizated by acetylhydrazide froups. J. Incl. Phenom. Macrocycl. Chem. 58, 55–61 (2007)
Podyachev, S.N., Sudakova, S.N., Syakaev, V.V., Galiev, A.K., Shagidullin, R.R., Konovalov, A.I.: The preorganization effect of the calix[4]arene platform on the extraction properties of acetylhydrazide groups with transition metal ions. Supramol. Chem. 20, 479–486 (2008)
Podyachev, S.N., Burmakina, N.E., Syakaev, V.V., Sudakova, S.N., Shagidullin, R.R., Konovalov, A.I.: Synthesis, IR and NMR characterization and ion extraction properties of tetranonylcalix[4]resorcinol bearing acetylhydrazone groups. Tetrahedron 65, 408–417 (2009)
Podyachev, S.N., Litvinov, I.A., Shagidullin, R.R., Buzikin, B.I., Bauer, I., Osyanina, D.V., Avvakumova, L.V., Sudakova, S.N., Habicher, V.D., Konovalov, A.I.: Structure and spectroscopic characteristics of 4-tert-butylphenoxyacetylhydrazones of arylaldehydes. Spectrochim. Acta. Part A 66, 250–261 (2007)
Podyachev, S.N., Sudakova, S.N., Syakaev, V.V., Shagidullin, R.R., Galiev, A.K., Konovalov, A.I.: Synthesis of tetrathiacalix[4]arene functionalised by acetylhydrazone fragments. Mendeleev Commun. 6, 297–299 (2006)
Podyachev, S.N., Sudakova, S.N., Syakaev, V.V., Burmakina, N.E., Konovalov, A.I.: Synthesis of new hydrazones based on tetrathiacalix[4]arene in the 1,3-alternate conformation. Russ. J. Org. Chem. 46, 1162–1166 (2010)
Podyachev, S.N., Burmakina, N.E., Sudakova, S.N., Syakaev, V.V., Konovalov, A.I.: Supramol. Chem. 22, 339–346 (2010)
Syakaev, V.V., Podyachev, S.N., Gubaidullin, A.T., Sudakova, S.N., Konovalov, A.I.: J. Mol. Struct. 885, 111–121 (2008)
Irving, H., Williams, R.J.P.: The Stability of transition-metal complexes. J. Chem. Soc. 8, 3192–3203 (1953)
Ikeda, A., Suzuki, Y., Yoshimura, M., Shinkai, S.: On the prerequisites for the formation of solution complexes from [60]fullerene and calix[n]arenes: A novel allosteric effect between [60]fullerene and metal cations in calix[n]aryl ester complexes. Tetrahedron 54, 2497–2508 (1998)
Asfari, Z., Lamare, V., Dozol, J.F., Vicens, J.: A tribenzo modified 1,3-calix[4]-bis-crown-6: A highly selective receptor for cesium. Tetrahedron Lett. 40, 691–694 (1999)
Budka, J., Lhotak, P., Michlova, V., Stibor, I.: Urea derivatives of calix[4]arene 1, 3-alternate: An anion receptor with profound negative allosteric effect. Tetrahedron Lett. 42, 1583–1586 (2001)
Iwamoto, K., Shinkai, S.: Synthesis and ion selectivity of all conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]calix[4]arene. J.Org. Chem. 57, 7066–7073 (1992)
Solovieva, S.E., Kleshnina, S.R., Kozlova, M.N., Galiullina, L.F., Gubaidullin, A.T., Latypov, S.K., Antipin, I.S., Konovalov, A.I.: Synthesis and complexation properties of carbonyl-containing thiacalix[4]arenes. Russ. Chem. Bull. 57, 1477–1485 (2008)
Acknowledgments
This work is supported by the Russian Fund for Basic Research (grant 09-03-00123-a) and the Deutsche Forschungsgemeinschaft (DFG grant GR 3296/1-1).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Podyachev, S.N., Burmakina, N.E., Syakaev, V.V. et al. Pyridinyl hydrazone derivatives of thiacalix[4]arene as selective extractants of transition metal ions. J Incl Phenom Macrocycl Chem 71, 161–168 (2011). https://doi.org/10.1007/s10847-010-9920-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-010-9920-3